Senior Software Engineer (Trust Foundations - Identity and Platform)

Building for trust is non‑negotiable in our mission of making mental healthcare more accessible and affordable across the US: patients share sensitive information, payers demand demonstrably strong controls, and providers depend on reliable, secure infrastructure. Trust Foundations is responsible for instilling confidence in our products by safeguarding our user’s data. We achieve this by developing out-of-the-box identity, access, and secure-data platforms for other engineering teams to utilize. Our mission is to make the most secure path the most efficient path, enabling clinicians, patients, and payers to trust Headway implicitly.

As a Senior Software Engineer on our Trust Foundations team, you’ll write production code every day while shaping the long‑term vision for trust at Headway. You will translate open standards - OAuth 2.0 / OIDC, RBAC/ABAC, envelope encryption - into scalable building blocks; embed privacy‑by‑design and reliability principles into everything we build; and mentor engineers across the company in Trust first thinking.

• Design, build, and operate core trust primitives - authentication providers, authorization engines, stratified encrypted data stores, and tamper‑evident telemetry.
• Embed security & privacy by design - Codify guardrails in linting rules and CI, and partner with Legal / Compliance to translate regulatory language into concrete engineering controls.
• Scale our identity rails -  Design and evolve multi‑tenant authentication & authorization services that handle millions of sessions daily with high availability expectations.
• Deliver scalable, secure platform foundations -  Build shared services that embed security‑by‑default (least‑privilege access, encryption in transit and at rest, audit hooks) and expose intuitive APIs so product teams can move quickly without compromising trust.
• Turn ambiguous requirements into incremental delivery plans - Lead architecture reviews; break large problems into testable milestones; and make pragmatic build‑vs‑buy decisions in a regulated domain.
• Champion operational excellence - Instrument services, tune alerting, own on‑call runbooks, and drive post‑incident hardening.
• Elevate engineering culture -  Mentor teammates, document patterns, and help recruit the next generation of Headway engineers.

• 5 + years of professional software engineering with a strong command of at least one modern language (we use Python 3 and TypeScript).
• Proven systems‑architecture leadership - you have shaped requirements, led cross‑team roadmaps, and delivered complex backend or platform services at scale.

Deep expertise in one of two focus areas:

• Identity and Access - demonstrated experience working with third party IdPs, expertise with OAuth 2.0 / OIDC standards, have implemented step‑up MFA and common RBAC frameworks.
• Platform Engineering (scalable, secure foundations) - demonstrated experience building high‑throughput, fault‑tolerant services that bake in security‑by‑default patterns, provide clear developer interfaces, and enable downstream teams to move faster.
• A track record of mentoring engineers, elevating design quality, and improving engineering processes.
• Sound build‑vs‑buy judgment and the ability to collaborate with product, legal, and operations in a highly regulated environment. 

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide.  The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

• Focus on the mission - We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapist to better solve the problems they’re facing.
• Ship small, learn fast - We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration.
• Everything is a product - Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
• Optimize for trust - We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

• Languages: Python 3, TypeScript
• Libraries & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js
• Datastores: Postgres, Redis
• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github, PagerDuty
• Vulnerability Management: Snyk, Semgrep
• Cloud Security: Lacework

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background. 
• First round: You'll meet with an engineer on the team to do some live coding and learn more about the engineering team.
• Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway.
• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

The expected base pay range for this position is $164,900 - $233,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

Equity Compensation

• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

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